Phosphorus oxychloride → 4-Chloro-1H-pyrazolo[3,4-b]pyridine

1,7-Dihydro-pyrazolo[3,4-b]pyridin4-one (1.2 g, 8.8 mmol) (Dorn, H. et al., Prakt. Chem., 324, 557-62 (1982)) in POCl3 (15 ml) at 0° C. was treated with PCd5 (2.5 mg, 0.01 mmol). The solution was allowed to warm to rt over 1 h, then heated to 90° C. and held 3h. The solution was concentrated under reduced pressure, then treated with ice and water (50 ml). The resulting mixture was extracted with ethyl acetate (100 ml), and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate (30 ml). The organic layer was dried over MgSO4, then evaporated under reduced pressure to give 4-chloro-1H-pyrazolo[3,4-b]pyridine as a yellow solid (820 mg, 60%). 1H NMR (300 MHz, CDCl3) δ 8.57 (d, 1H, J=5.2 Hz), 8.25 (s, 1H), 7.28 (d, 1H, J=5.2 Hz).

1. temperatureheated to 90° C.
2. concentrationThe solution was concentrated under reduced pressure
3. additiontreated with ice and water (50 ml)
4. extractionThe resulting mixture was extracted with ethyl acetate (100 ml)
5. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate (30 ml)
6. dry with materialThe organic layer was dried over MgSO4
7. customevaporated under reduced pressure

ORD record

ord-c7861cf32f8c430d84b4a51baaf34537

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06531491B1